"Every day you’re not showing up, you’re robbing people of something they need—and only you can give it."
— Kyree Oliver
In a world obsessed with credentials, production value, and follower counts, it’s easy to forget that real transformation doesn’t come from how flashy your funnel looks. It comes from you. The real you. That was the heartbeat of the conversation between Amanda Kaufman and Kyree Oliver—an unfiltered, grounding dialogue about identity, visibility, and coaching from a place of authenticity, not performance.
This episode wasn’t recorded in a polished studio or on a big stage. It was a raw, real-time conversation from a hotel lobby—two coaches deeply invested in the human experience, exchanging stories, ideas, and truth bombs that every heart-centered entrepreneur needs to hear.
Let’s dive into the core ideas that make this episode one of the most important listens for any coach or leader struggling with visibility, imposter syndrome, or the pressure to “play the part.”
Kyree’s story starts where many powerful ones do: with an identity crisis.
He had just walked away from his dream of playing in the NFL and found himself asking, “Who am I now?” It’s a question most of us don’t ask until life forces us to. But instead of avoiding the discomfort, he leaned in—interviewing over 1,000 people from monks to billionaires in a quest to understand how identity shapes everything we do.
His conclusion? Most people don’t know who they are. They’ve never taken the time to articulate it. And if you don’t know who you are, how can you show up fully for anyone else?
As Kyree put it: coaching didn’t come from getting trained in coaching. It came from studying psychology, philosophy, and watching how people tick. The role of coach was something that unfolded because he lived it—not something he forced.
There’s a line Kyree shared that will stay with you:
“Most coaches are playing a role. I’m not playing a role. I’m just being me.”
In an industry where so many people are chasing authority by faking it until they make it, Kyree offers a radically different path: Be exactly who you are. Let people see it. And stop thinking you need more proof before you’re allowed to help someone.
For Kyree, coaching isn't about creating distance or dressing things up for the camera. His clients come to his house. They meet his wife. They see who he really is—not just his branding.
That authenticity isn’t just refreshing; it’s powerful. Because when people encounter someone who’s actually living what they teach, trust forms quickly. Connection deepens. Transformation follows.
Amanda brought vulnerability into the conversation when she shared how long it took her to fully own her role as a coach. Like many, she chased certifications and read all the books—but still didn’t feel “qualified.”
“I was looking for a permission slip no one could give me.”
That’s a line so many can relate to.
The truth is, certifications can be valuable. So can experience and education. But none of that replaces the deeper qualification of being someone who truly listens, embodies what they teach, and creates meaningful relationships. At the end of the day, coaching is about presence, not perfection.
Perhaps the most mind-blowing revelation? Kyree built a multi-six-figure coaching practice without a funnel, landing page, or automation for years.
It was all organic. All relationship-based. Referrals, conversations, and his commitment to impact.
Now, is there a place for automation and systems? Of course. But Kyree’s story serves as a bold reminder that you are the asset. Your voice, your values, your integrity, your ability to deeply serve others—that’s what grows a coaching business that lasts.
He only started building funnels recently—not because he “had to,” but because he wanted to make his message more scalable. That’s a huge shift from the pressure many new coaches feel to start with the tech stack and automation before they’ve even shared their first message.
The most powerful idea from this episode was the concept of robbing people by not being seen.
When you hide, play small, or minimize your impact, you don’t just slow down your own journey—you withhold something others might desperately need.
“If you don’t say it, someone who needed to hear it won’t.”
That’s not about vanity metrics or social clout. It’s about service. If you believe what you do matters—if you’ve seen lives change because of your work—then it becomes an act of service to show up boldly.
Authenticity doesn’t require a spotlight. It requires courage. The courage to post the message even if it doesn’t go viral. To host the event even if 3 people show up. To speak the truth even when it’s not trendy.
That’s what this episode celebrates.
As Amanda shared in the conversation, she once referred to her podcast as her “little show”—until a mentor stopped her in her tracks and said, “Don’t ever call it that again.”
That was a turning point. From that moment, it wasn’t “her little show.” It was The Amanda Kaufman Show.
We don’t need to wait until the results look impressive before we allow ourselves to own the impact. Let it be what it is. And what it is... is powerful.
If there’s one takeaway from this episode, it’s this:
Stop waiting to be seen. Your people are already looking for you.
00:00 Introduction and Background of Kyree Oliver
03:08 The Journey to Coaching and Identity Crisis
05:53 Philosophy and Approach as a Coach
08:49 The Importance of Authenticity in Coaching
12:11 Building a Coaching Business: Surprises and Insights
15:06 Advice for Aspiring Coaches and Conclusion
Amanda Kaufman (00:01)
Well, hey, hey, welcome back to the Amanda Kaufman show. Ree Oliver, what a pleasure. Oh, thanks for joining. Oh my gosh. So this is such a special episode because we're sitting here in a hotel lobby, getting to meet person at an event.
Kyree Oliver (00:09)
Thank you.
Amanda Kaufman (00:18)
Do you want to take like 30 seconds and tell us a little bit about your background, what it is you do?
Kyree Oliver (00:23)
Gosh, that's always hard. So I'm an ex-debitionary football player. I started a marketing company team. I only started that marketing company to give me credibility when I came to coaching. I knew I wanted to help people. I didn't know how. I didn't know what it was going to look like. I was 19, 20 at the time. ⁓ And I knew I needed real life credibility in order for people with money to trust me enough to help them with their personal lives. So I figured I would help them with their businesses first and figure out a good skill to help them with their businesses. In the meantime,
I was building my company. was interviewing, I interviewed over a thousand people from monks to billionaires to any type of person would probably think of. I've interviewed somebody of that type. And I was just obsessed with why we are the way we are. What creates our identity. That leads to our beliefs, our habits, our behaviors, everything underlying. And then when I was 24, I actually said I wouldn't start coaching until I was 30. Luckily I started very early, started at 24 years old.
Mostly just coaching young guys and I still typically work with younger guys. I just turned 31. Most of my guys are between 20 and 35, but I have a 46 year old woman who works here right now. I've got a 50 year old man who works for me right now. ⁓ Mostly entrepreneurs, but some more like blue to white collar people work for as well. And I just help them figure out the stuff that goes on in their heads. I help them change the internal conversations they're having with nobody else's group.
Amanda Kaufman (01:45)
love that. I love how you put that. And you knew so young. Like I'm thinking, what was I doing at 19? You definitely not playing football. For sure aware yet of the personal development world or mindset. I walked a very different path to kind of get to the same place where I'm obsessed with psychology and the philosophy and applying that in your life so that you can make
better decisions and live in your highest potential and in your highest character as well along the way. So I'm just so curious, like 19, like was there an inflection point or a moment that told you like, wow, I really want to be me. I want to have that role in people's lives.
Kyree Oliver (02:28)
Yeah, it was first for myself. It selfish thing first. I was trying to figure out who I was. I'm done playing football. I was thinking about quitting playing football. I'm no longer going to be an NFL player, and that's the only thing I'd ever thought of being. And so then, who am I now? And I went through this whole early, thankfully early, identity crisis. I thought it was the worst thing in the world. And then I started seeing the people in their 30s, 40s, 50s going through their own identity Prices?
And I realized how much of a blessing it was to be going through it before I have a career, family, kids, a wife, anything like that. So I just chose to like, here, let me just jump in and embrace this version of it. And I don't know what it looks like. I don't know how I help people. I know it's supposed to help. I know there's just something I built for. I don't know exactly what it looks like. And I kind of have just painted in the details along the way.
Amanda Kaufman (03:14)
You know, I have the pleasure of getting to meet you by I was in the mastermind and we kind of met in the same place and sort of have similar circles. But I was impressed right away with your I would say you do have a very like calming philosopher vibe. just like the way you talk about the decisions that people made. I'm so curious, like when you decided to activate 24, you know, like embrace it, I'm to be the coach, I'm going to do it now. Yeah.
⁓ What what cost you to decide to do it a little earlier than you thought?
Kyree Oliver (03:46)
Somebody I talked to, he said, every year, every month, every day, every hour, you're not doing this. You're robbing yourself and other people of some sort of magic, of something they're supposed to have that they're otherwise not going to have it because you thought it was too soon. And basically just saying, let the market decide if you're too soon. People have to hire you if you're too early. I've always had this thing of I'm too young. Even in my marketing company, I didn't tell people how old I was. All I'd let this was my results. Here's what I've done for other people. I'd love to do it for you as well.
I told them I was 20 or 21. I even had me to find out later how old I was. They're like, oh, thank you for not telling me. I would have never hired a kid to do this for me. And so I think I just had that in my mind. And it just helped me drop that. Like you're actually robbing people of something by not doing this. It felt more like a positive obligation. I don't say obligation, it's a negative thing. But it felt like I'm full of mind and not a thing.
Amanda Kaufman (04:39)
I really love that. How often are we the first person to be discerning on ourselves? And what we can do. And like even just this show, you know, I had the pleasure of getting to work with Tom Bilyeu earlier this year. It was insane. I went to his house and I was just like, what is this plan I find myself on? was such a tremendous honor. And he asked me like what I was working on, what was going on. And I referred to my show with my little show. I said, you never do that again. It was the most
Direct Kurt thing ever and I was like honestly shocked by it and but it changed everything because When I was like no, this is my show. My name is on it. It's my show It's not defined by the number of downloads. It's not defined by episodes. It's not defined by you know current production quality and all these things that I was discounting myself and my own creation It's not my little show. It's Game Man the Kaufman Show
Kyree Oliver (05:34)
Yeah, at that point you're not allowing it to be what it is, right? Making it be something smaller. And then when you drop that book, sometimes you won't drop that until you have what? million sound books and then you'll be able to talk about it as a show. You're gonna increase the battery on that. just allow things. Yeah, let it be what it is.
Amanda Kaufman (05:52)
Let it be what it is. Yeah, I love that so much. Talk to me a little bit about your philosophy as a coach. Like, what do you really try to do against somebody? what, I guess what makes you unique as a coach? What do you think is your angle?
Kyree Oliver (06:08)
I don't think I have an option because I don't, I didn't learn coaching. I learned psychology. I learned philosophy. Again, how I take it and then I learned how other people think and why would you do it? I didn't learn how to coach. Coaching was the natural progression of, I just understand a lot of these things and I don't think most people understand that while I don't have the life experience or my life experience is happening at the same time as I'm growing, I'm helping other
I think I just have my finger on the pulse of people really well. And so I think the uniqueness is in the closeness I continue having with us as people. I still do volunteer work. I still work with youth. I still work with businesses of all sizes. I hang out with billionaires as well. A few of my clients are selling their companies for multiple nine figures right now. But again, work with startup entrepreneurs and I work with teenagers.
I just have my pulse on so many different types of people. constantly feeding this knowledge base, let's say, in my own head of why we are the way we are. So when people say they want to be something, I find that most people don't know who they currently are. And they haven't articulated it to themselves. And they haven't really searched and done for that. So that's where everybody starts. I start everybody off with, I call it my identity. My next session, my next session is a connection between two points. How you identify who your correct self is. I have you connect that to your future self.
And I just helped you walk down that path or I helped you create a bridge between the two and literally communicate with your future self. Cause what people started realizing during that process is if I'm able to say this to myself as me in 20 years, it must already be in here. I must already have access to it. I just haven't given myself access to it. Just like the talk about with your little show, keep calling your little show, it'll never just be your show and whatever size it is. And so I want people to be able to articulate who they are and who they're trying to become. But when they're pulling from that future self to their current self,
They're actually gaining some sort of access. They're actually like, you know, folding space time kind of thing. I don't do the whole content. This is actually a quantum person right over here. I heard she made a table, but I hope people kind of do that and bridge that gap for themselves. So here's who you are, here's who you're looking at. You can actually shorten that gap by the bigs. You just never sat down and really dug into this person.
Amanda Kaufman (08:24)
So good. You know, I'm thinking about the phrase know thyself. I really believe know thyself as an ongoing opportunity for life. That's what you're always doing. Daily practice, exactly. You know, coaching and the whole coaching. I myself, got a certification. And it was so funny because like you, I love to read. I'm studious, so I was reading.
psychology and sociology and philosophy and like all these kinds of things and I still didn't feel good enough. Yeah. You know, to call myself a good person. I think it was extra serious. It's kind like the same thing you went through when you're 24. What if they don't take you seriously?
Kyree Oliver (09:06)
There's
this analogous, it doesn't actually exist today. Nobody's actually ever told me that.
Amanda Kaufman (09:11)
Who
is the thing? What would you say to someone they feel that their future identity is to play that role of coach of that person? What do you think really matters to pursuing that?
Kyree Oliver (09:27)
I
think not playing a role is the first one. I think most coaches are playing a role. This is where I get sticky with most coaches. They're fluent, like this is I don't allow myself to be called a mindset coach. If somebody calls me a mindset coach, I'll correct them. I don't call myself a mindset coach. I think mindset coaches are filling the roles. They're telling you how to think about something that they don't necessarily try to think about. I leave my example. I have my clients over to my house, my clients being my children, my clients being my wife.
My class coming by poker night on Wednesdays and I the old guys that I hang out with and tell raunchy jokes with. They have been to the billionaire's houses that I hang out with in Spotsville. They are immersed in my life in some way. I need to show people this is actually what it looks like. This isn't a show. This isn't the role that I'm playing. This is who I actually am. And it's also not like this big giant glamorous thing either. It's not this fictitious world that you've created.
This is a realistic version of me that I just get to live out throughout my life. But it's something I started planning 12, 13 years ago. So one, think, is the biggest thing is stop trying to play a role. Stop trying to be too smart. Stop trying to get all the athletes under your belt before you can get it. Have to actually be on the first seed. Or the type of clients everybody's looking for will absolutely completely run away from you. And that's what I find with a lot of coaches, or a lot of people are trying to a role. They're actually on field science.
It's far, far away from that. And they typically can't even tell them why they didn't hire them. Why that sales call didn't work out. Things are feeling, something was off or something didn't feel there. Whereas when I thought people constantly, I just get it. You're the person I thought, or you're a better version of what I thought you were saying. Something's online, something I don't like, and then I'm the tech person. And so when you can tell they're genuine, just get a lot more genuine.
So my advice would be, act just second to being the person. Stop trying to your role and think that you'll gain the fight over to become successful out there.
Amanda Kaufman (11:33)
I do not expect you to remember this, but a couple years ago when we met, I said that you have a certain gravity. And I think that that's what it is. I don't agree with you on some of the things that you said, just like, I said that to you like two years ago and you're like, amazing. We can have that conversation. I'm like, amazing, okay. You know, my experience with you is that you are incredibly intelligent.
Kyree Oliver (11:48)
That was our first conversation.
Amanda Kaufman (11:58)
And you're so respectful, yes, like for the tactics to change perspective shift. And I love what you're saying about, you know, embodying, not playing the character, but actually embodying character, not the character, but what are those characters? I love that.
And you know, speaking as the coach, was oh, not good enough to get this certification. actually, that certification is a weird. You're getting the science fact certification. You know, I was chasing something, I think, is congruent. It's a love understanding. you know, I love that. But when I realized that they served the case, was essentially like a book, more information. But that's the way that I would from a book, it just a different kind of experience. It didn't necessarily qualify me more.
to have the kinds of relationships that a country has have. Coach, the end of the day, in my opinion, it's a relationship. That's all it is. Yeah.
Kyree Oliver (13:04)
I think for a lot of people, in the kind of trying to the role of saying it, most people do.
Again, I think they're looking for permission that they'll run up to to forgive them, which is the problem. And I think this is why people get overqualified for something. They'll become overqualified and they'll be ineffectualized in compliance. Looking for a permission slip that nobody can give them. You have to give yourself that. You can only give yourself that when you're comfortable with this post-it. And I think a lot of use their clients as their own therapy before they try to tell the client what they need to hear. But just generally, it's not about...
When I'm in a coaching session, it's not about building anything. I'm then open to overflowing my own power. To give the extra, I give the extra. I'm gonna end first. I think that's a hard thing for coaches to do. Because I can't today, like, who are making revenue, who are generating business from it. And so it's hard to kind of separate us to a time. But it has to just be, that's like, has to be because this is who I am. I couldn't not do this. That's the only reason it works.
Amanda Kaufman (14:14)
I'm about something, you know, they're listening in to the show right now and they're hearing us talk about this and they're like, yeah, yeah, yeah. You're getting the checklist of what to do. But I'm also thinking about that metaphor of, you know, reading the books on how to swim versus getting in the water swimming. You know, when I started my business, I've had eight meetings on a post-it of people that I felt vulnerable enough to get to reveal that I wanted to do this coaching business.
And, you know, I had contacts on LinkedIn and I had a small Facebook account at the time, but I just, didn't feel the ability yet to have vulnerability with people in a broader sense than those eight. So that's where I started. I just felt those eight people. And that was a, was so funny because like one of the, one of the first guys that I've been in complimentary with was like, is amazing. Can I ask you a question? I this friend Bob.
Bob's like, going through a thing, thinking about changing his job. And it literally, until that point, hadn't occurred to me. But even though I had a really small number that I felt vulnerable with, other people who were there, and your network has a network. And I feel so blessed and fortunate. It feels like serendipity still, with everything that I've learned since then. To just get that gift, and somebody's like, hey, I introduced you.
It wasn't, I introduce you because you have certain letters after your name? Can I introduce you because you've impressed me with this particular exercise we did. It was just, wow, I felt like this was really good for my.
Kyree Oliver (15:52)
Introducing that that is it. I've been since he's still mostly referrals I mean, it's organic as I most thought of concept but mostly we his friend of her friend I find it mine had mentioned me to somebody else I just set up a meeting right before being sat down with somebody who's friends of former client line It's actually his ex-girlfriend a good friend of mine was also a coach they've been traveling friend mentioned to me was like, dude I said I've got something I think when I've started issues with this, let's you should be talking to him
And those are the types of connections that just happen pretty constantly. And it's barely when you're actually doing it again, the right thing or in the right way, that they are willing to be committed to someone else. Because for a lot of people it's embarrassing to talk about having a church. Not so much in our world, like in the online business, marketing, personal development. It's accepted here. It's almost like saying you have a church for a lot of people.
Amanda Kaufman (16:37)
receptive here. ⁓
Kyree Oliver (16:42)
But when they're at that level and then their network notices the changes in them, they can't help but say, yes, I did the work. Yes, I've done this, but this guy helped me quite a bit. But this will be helped quite a bit. And I think that's how it's supposed to roll.
Amanda Kaufman (16:56)
I think I totally agree and I have a very similar experience with that. I am very curious on the business side of building a coaching business. What did you find the most surprising along the way? What turned out different than you thought?
Kyree Oliver (17:12)
about building, actually, how much you to me was so little. Like I don't have infrastructure in my business. I'm actually building it right now. At this event, I'm back and forth with my team on building my first actual funnel and building my Managed Chat Automations. I didn't know I could go this far without doing it. I thought genuinely, I'll make $10,000 to $12,000 a month doing this, and then I'll have to get into this stuff and then I'll get into building. And I've been now, you know,
seven years in, almost eight years in, and I'm just now setting up these sequences and out of convenience really it's just me. Okay, it's time and I want to make what I do with what I say more valuable to more people that can't afford to work with me personally, so I just might as well do it. It's not out of necessity, it's not I have to do this to make my business survive. So how far you can go with literally nothing else other than your words and your ability to impact other
Amanda Kaufman (18:08)
You know, my motto is do what matters. And it's so funny because it has to be my motto because I have to remind myself to do it because I'm very curious and I want to do everything and I can be a bit of a tornado. And it's so funny because we're at the same event and I'm just cutting away. I'm like stripping it all away because I think...
there's a notion in our space that you're not good enough unless you have all these systems and you're doing these big guru events and everything. And it's like, well, what's the business you're building? There's nothing wrong with becoming a guru in my opinion, but what's the business that you're building and what's the leverage that you have right now? And I hope, dear listener, you just heard him say he's doing this and very happy with the revenue for seven years before even thinking about doing a phone. Yeah. Yeah. That's so good. That's so good.
If you have the opportunity to whisper one piece of advice into a serious, authentic, character-driven approach, like whisper into their ear, what would you say to
Kyree Oliver (19:05)
authentic character driven approach. You almost all, you have to talk more about what you're actually doing. I think people shy away and I'm specifically talking about the character driven approach. Because again, it's not the fanatic approach, it's not the Google online, it's the person who's genuinely out there to serve. I feel like they have a really hard time talking about what they actually, or people, or being able to share, not necessarily providing information about the clients, but like what changes they're helping.
And that's the only way other people hear much but you have to have eyeballs on what you're or else I can you robbing robbing people by not getting your voice or name out there much and That still feels authentic right? It's not needing to go viral with everything that you're posting or needing to be Opposition of confrontation just so that you know more comments or whatever but being willing to just
Amanda Kaufman (19:56)
We will like to see I love that. Harry, how could people follow you to catch up with you? What's the best way to do that?
Kyree Oliver (20:04)
Instagram or Facebook? Instagram is just at Kyrie, K-Y-R, Facebook, I don't know, a link. Yeah, so I'll send it to you. This is Kyrie Oliver. I'm the big brown guy with tattoos at PomSum.
Amanda Kaufman (20:10)
Put a bit in the showdown.
I love it. love it. Is there anything else you'd like to share before we wrap it up? Amazing. Wonderful conversation. Thank you. Thank you. All right. Dear listener, don't forget to subscribe if you haven't already. Make sure you grab a link to this episode. Share with at least three of your coachy friends. They really need to hear that the best version of their coaching business is them sharing up with their best version of themselves. And you know, if you really loved it, Tyree did an amazing job. Go ahead.
Kyree Oliver (20:21)
No, good. Thank you.
Amanda Kaufman (20:46)
And leave us an authentic review. And you know, those five star reviews, they help people choose us when they're out for a walk, but we really appreciate it. We'll see you the next time. No matter.